Start Your Route 66 Road Trip in Chicago

Route 66 is the road people picture running through the desert West, but it starts in downtown Chicago, a couple of blocks from the lake. From there it runs about 2,400 miles to California. It was designated on November 11, 1926, so 2026 is its centennial year, and Illinois has spent the year celebrating.

If you're looking for summer road trip ideas, this one is hard to beat. Spend a few days in the city, then pick up a rental car and head southwest.

Finding the start

The route's history explains why there are two signs. The original 1926 route ended at Jackson Boulevard and Michigan Avenue. In 1938 it was extended two blocks east along Jackson, past Buckingham Fountain, to Lake Shore Drive. Then in 1955 Jackson became a one-way street heading east, so westbound Route 66 moved one block north to Adams Street.

That's why the "Begin Historic Route 66" sign is on Adams Street, just west of Michigan Avenue. The "End" sign for drivers coming the other way is on Jackson at Michigan. Both are easy to find on foot from Millennium Park, and a photo with the Begin sign is the traditional first shot of the trip. Try it early on a weekend morning, when the Loop is quiet.

In March 2026 the city added a third spot. A new sign outside Harry Caray's Tavern at Navy Pier now marks a "symbolic" start for the centennial, WBEZ reported. The link is Harry Caray, who, as WBEZ tells it, traveled Route 66 to announce his first game in 1945. It's a fun stop if you're at the pier, but the Adams Street sign is the real one.

Breakfast first

Lou Mitchell's (565 W. Jackson Blvd., near Union Station) has been serving breakfast since 1923, and it's known as "the first stop on the Mother Road." Get eggs or pancakes. Since 1958, the staff have handed out donut holes to people waiting in line, and Milk Duds are part of the tradition too. It's open 6am to 2pm Wednesday to Friday and 7am to 2pm on weekends, and it's closed Mondays and Tuesdays, so plan your departure day around that.

If you'd rather start with lunch, The Berghoff is right on the westbound route at 17 W. Adams St. It's been serving German food since 1898, according to Choose Chicago, and it brews its own beer.

Getting out of the city

From the Loop, the route heads west on Adams (or Jackson, coming in), then turns southwest onto Ogden Avenue. Ogden cuts diagonally through the West Side, past the Illinois Medical District, the Tri-Taylor neighborhood, Douglass Park and Lawndale, and into Cicero and Berwyn. The city has put up wayfinding signs along Ogden, and Lulu's Hot Dogs in Tri-Taylor has a new Route 66 mural and photo backdrop. Berwyn has its own Route 66 museum on Ogden.

From Berwyn the old road follows Joliet Road through Lyons and McCook, where a quarry forced a detour in 1998, and the signs will steer you around it. West of Indian Head Park, I-55 was built over much of the old road, though a frontage road in Darien, Willowbrook and Burr Ridge keeps some of the old feel. In Willowbrook, Dell Rhea's Chicken Basket has been frying chicken on Route 66 since 1946, and it's listed on the National Register of Historic Places.

What's along the Illinois stretch

Illinois has 301 miles of Route 66, from Chicago to the Chain of Rocks Bridge over the Mississippi. Heritage Corridor Destinations, the tourism group for the northern end, calls its part of it "The First Hundred Miles." Here's what to stop for, north to south.

• Joliet. The prison gates from The Blues Brothers at the Old Joliet Prison, and the 24-foot Gigantar sign outside the Illinois Rock and Roll Museum.
• Wilmington. The Gemini Giant, a 30-foot fiberglass astronaut holding a rocket, now stands in South Island Park, and there's a Route 66 souvenir shop called The Landing Pad a few steps away.
• Dwight. Ambler's Texaco pumped gas for 66 straight years, until 1999, which makes it the longest-running gas station on the route.
• Odell. A Standard Oil station from the road's heyday.
• Atlanta. The American Giants Museum, which opened in 2023, is all about the fiberglass "Muffler Man" statues that used to stand outside roadside businesses.
• Springfield. The state capital is the Route 66 town with the most to see. The Cozy Dog Drive In (2935 S. Sixth St.) sells the cornmeal-battered hot dog on a stick that Ed Waldmire started selling at the Illinois State Fair in 1946, according to Wikipedia. Shea's Gas Station reopened as a Route 66 museum in 2024, Motorheads has what it calls the world's largest Route 66 sign, and the Legends Neon Sign Park at the state fairgrounds recreates the signs of old Route 66 businesses. At Carpenter Park, a quarter mile of original 1920s pavement has been restored for walking.
• Litchfield. The Ariston Cafe is on the National Register of Historic Places and still serves meals.
• Granite City. The town has been adding supersized roadside sculptures, including two new Muffler Men and a 20-foot metal fork, plus the It's Electric neon sign park.
• The Chain of Rocks Bridge. The 1929 bridge over the Mississippi has an odd 22-degree bend in the middle. It closed to cars in 1967 and has been open to walkers and cyclists since 1998, so park and walk across into Missouri.

How Illinois marked the centennial in 2026

The state set up an Illinois Route 66 Centennial Commission, which says Illinois was the first state to pave its entire stretch of Route 66. Its 2026 program listed the Red Carpet Corridor festival in May, in towns between Joliet and Bloomington, and a Great Race classic car rally starting from Springfield in June. Chicago added the Ogden Avenue signs, the Lulu's mural and the Navy Pier sign. On November 11, 2026, the 100th anniversary of the route's designation, Springfield hosts a Route 66 Centennial Conference, with an evening gala at Motorheads. Springfield's International Route 66 Mother Road Festival, with vintage cars and live music, runs every September. For current events, see Enjoy Illinois.

Beyond Illinois

From the Mississippi, the road runs through Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California. That means St. Louis, Tulsa, Oklahoma City, Amarillo, Albuquerque and Flagstaff. See the Arch in St. Louis (what to do in St. Louis), eat something with New Mexico chile in Albuquerque, detour to the Grand Canyon from Flagstaff, and stop in the small towns in between. Our BootsnAll list of the weirdest roadside attractions in America has a few more ideas.

You don't have to drive all of it. Pick a section and turn back, or fly to the far end and book a one-way rental home. With only a weekend, a run down to Springfield and back covers the best-known Illinois stops. For other ideas close to the city, see easy day and overnight trips from Chicago.

Photo by Michael Kesler